US20090131519A1 - Use of Growth Regulators for Reducing or Preventing the Contamination of Plants and Vegetable Products by Trichothecene-Producing Mould Toxins - Google Patents

Use of Growth Regulators for Reducing or Preventing the Contamination of Plants and Vegetable Products by Trichothecene-Producing Mould Toxins Download PDF

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US20090131519A1
US20090131519A1 US11/988,474 US98847406A US2009131519A1 US 20090131519 A1 US20090131519 A1 US 20090131519A1 US 98847406 A US98847406 A US 98847406A US 2009131519 A1 US2009131519 A1 US 2009131519A1
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plants
compounds
trichothecene
plant
contamination
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Wilhelm Rademacher
Veronica Companys
John-Bryan Speakman
Helmut Merrmann
Dieter Strobel
Martin Semar
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BASF SE
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Definitions

  • the present invention relates to the use of growth regulators selected from acylcyclohexanedione derivatives and quaternary ammonium compounds for reducing or preventing the contamination of plants and plant products with mycotoxins formed by trichothecene-producing fungi.
  • the harvested material of all cereal species such as wheat, barley, rye, triticale, oats, rice and corn, and also that of many other plant species, such as potato, sugar beet, tomato, pea, leek, asparagus, fodder grasses and fodder clover, can be contaminated with trichothecene toxins and other mycotoxins which originate from trichothecene-producing mold fungi. Most highly affected are triticale, oats, common wheat and in particular durum wheat. The source of these toxins are certain fungi, for example those of the genera Trichoderma, Stachybotrys and in particular Fusarium , infecting these plants.
  • Fusarium fungi results in a characteristic ear infection where individual ears are bleached and in some cases a reddish spore coating can be observed. In most cases, the ears dry out above the infected site, and only a shriveled grain is formed there. It may well be possible that normally sized grains mature below the infected site; however, these are generally contaminated by fungus toxins. Accordingly, Fusarium fungi may not only reduce the yields, but, in particular, they also contaminate the harvested cereal with mycotoxins. Contamination of the cereal grains may take place both in the ear and during storage of the harvested material.
  • growth regulators do not have any fungicidal action.
  • certain compounds having a N-containing heterocycle and having a certain fungicidal activity i.e. growth regulators of the triazole type (for example paclobutrazole and uniconazole), of the pyrimidine type (for example ancymidole and flurprimidole) and of the 4-pyridine type (for example inabenfide) are an exception (W. Rademacher, “Growth retardants: Effects on gibberellin biosynthesis and other metabolic pathways”, Annual Review of Plant Physiology and Plant Molecular Biology 51, 2000, 501-531).
  • acylcyclohexanedione compounds prohexadione-Ca and trinexapac-ethyl may induce resistance against attack by pathogens in certain plant species.
  • U.S. Pat. No. 6,022,831 describes the use of acylcyclohexanediones against infection with fire blight ( Erwinia amylovora ) in pome fruit.
  • WO 00/78144 describes the use of acylcyclohexanediones for increasing the resistance of crop plants against infection with certain phytopathogenic fungi.
  • the growth regulators mentioned inhibit the biosynthesis of these toxins. However, it is also possible that, additionally or alternatively, they induce or increase the resistance of the plants against attack by pathogens.
  • C 1 -C 10 -alkyl is a straight-chain or branched alkyl radical, such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl or decyl.
  • alkyl radical such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl or decyl.
  • C 1 -C 4 -alkyl is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
  • the alkyl radical is preferably straight-chain.
  • C 3 -C 10 -cycloalkyl is, for example, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl or decalin.
  • C 3 -C 6 -cycloalkyl is, for example, cyclopropyl, cyclopentyl or cyclohexyl.
  • Halogen is preferably fluorine, chlorine or bromine and particularly preferably chlorine. Accordingly, halide ions are preferably fluoride, chloride or bromide and particularly preferably chloride.
  • Sulfate ions are both the bare sulfate anion SO 4 2 ⁇ and C 1 -C 10 -alkyl sulfate ions RO—S(O) 2 —O—, in which R is C 1 -C 10 -alkyl, for example methyl sulfate, ethyl sulfate and the like.
  • R is C 1 -C 10 -alkyl, for example methyl sulfate, ethyl sulfate and the like.
  • Preferred is the bare sulfate anion SO 4 2 ⁇ .
  • C 1 -C 10 -Alkyl sulfonate ions are anions of the formula R—S(O) 2 —O—, in which R is C 1 -C 10 -alkyl, for example methylsulfonate, ethylsulfonate and the like.
  • Borate anions are preferably those of the formula III
  • M is preferably a cation of a metal selected from the group consisting of sodium, potassium, magnesium, calcium, zinc, manganese and copper, is a proton or is ammonium.
  • A is preferably selected from the group consisting of hydroxycarboxylic acids, carboxylic acids, alcohols, glycols, aminoalcohols, sugars and the like.
  • Suitable hydroxycarboxylic acids are, for example, glycolic acid, lactic acid, mandelic acid, malic acid, tartaric acid, citric acid, other fruit acids and also hydroxyfatty acids, such as ricinoleic acid.
  • Suitable carboxylic acids are monocarboxylic acids, such as formic acid, acetic acid, propionic acid, valeric acid, isovaleric acid, caproic acid, enanthic acid, caprylic acid and other fatty acids, and dicarboxylic acids, such as oxalic acid, malonic acid; succinic acid, adipic acid and the like.
  • Suitable alcohols are, for example, C 1 -C 8 -alcohols, such as methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, pentyl alcohols, such as pentanol and amyl alcohol, hexyl alcohols, such as hexanol, heptyl alcohols, such as heptanol, and octyl alcohols, such as octanol and 2-ethylhexanol.
  • C 1 -C 8 -alcohols such as methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, pentyl alcohols, such as pentanol and amyl alcohol, hexyl alcohols, such
  • Suitable glycols are, for example, C 2 -C 10 -diols, such as glycol, diethylene glycol, triethylene glycol and the like.
  • Suitable aminoalcohols are, for example, ethanolamine, diethanolamine, triethanolamine and the like.
  • Suitable sugars are, for example, pentoses and hexoses, such as fructose, glucose, mannose and the like, and also disugars, such as sucrose.
  • x is preferably 0, in particular if M does not have one of the preferred meanings mentioned above.
  • y is preferably a number from 2 to 20, particularly preferably from 2 to 10, more preferably from 3 to 10, even more preferably from 3 to 7 and in particular from 3 to 5. y is especially 5.
  • z is preferably a number from 6 to 10, particularly preferably from 6 to 8 and in particular 8.
  • v is preferably 0.
  • w is preferably a number from 2 to 10, particularly preferably from 2 to 8 and in particular 2 or 3.
  • m is preferably 1 or 2 and in particular 1.
  • borates of the formula (III) in which y corresponds to a number from 3 to 7, in particular from 3 to 5; z corresponds to a number from 6 to 10, in particular from 6 to 8; v is zero; and w corresponds to a number from 2 to 10, in particular from 2 to 8.
  • the charge is compensated via the cation M.
  • the borates may comprise water, for example as water of crystallization in free or coordinated form or as bound water in the form of hydroxyl groups attached to boron.
  • Suitable and preferred borates and processes for their preparation are known per se and described, for example, in WO 02/083732 and in the literature cited therein, the entire content of which is incorporated herein by way of reference. Further suitable borates are described, for example, in WO 99/09832, the entire content of which is incorporated herein by way of reference.
  • the toxins formed by trichothecene-producing fungi are both trichothecenes and toxins different therefrom originating from the same mold fungi.
  • the trichothecene-producing fungi are preferably those of the genera Trichoderma, Stachybotrys and, in particular, Fusarium.
  • Trichoderma In the case of the genus Trichoderma , it is in particular the representative Trichoderma viride which is of importance in this context.
  • the mold fungi of the genus Stachybotrys are in particular Stachybotrys chartarum.
  • the mycotoxins are in particular trichothecenes or zearalenone.
  • Zearalenone is a mycotoxin with estrogen action which is formed by various species of the genus Fusarium .
  • Preferred substrates of the zearalenone-forming fungi are corn and oats.
  • other cereal species may also be heavily infected.
  • zearalenone is formed in a very late development phase of the fungus, it is found especially in highly infected cereal.
  • Zearalenone has no acute toxicity; however, it is presumed to have carcinogenic action. In grazing animals, it causes fertility disorders, premature births and stillbirths.
  • trichothecene refers to a group of about 100 mycotoxins formed in particular by fusaria, but also by other mold fungi on plants and plant products, in particular on cereal and cereal products. Trichothecenes have a broad spectrum of biological actions. In general, trichothecenes inhibit the protein biosynthesis in mammalian cells, sometimes even at concentrations as low as 1 ng. Trichothecene poisoning causes vomiting, diarrhea, food refusal, inflammations of the gastrointestinal tract, damage to nerve cells, heart muscle, lymph system, testes, thymus and development of tissue necroses.
  • Poisonings of animals and humans are known, for example, under the term “moldy corn toxicosis” (USA), “bean hull toxicosis” (Japan) or “alimentary toxic aleukia” (CIS). According to their chemical structure, the trichothecenes are divided into groups A to D.
  • DAS diacetoxyscirpenol
  • DON deoxynivalenol
  • 3-acetoxynivalenol 15-acetoxynivalenol
  • fusarenone T-2 tetraol and verrucarol.
  • Plants in which the formation of the mycotoxins mentioned is to be reduced or prevented are preferably selected from the group consisting of cereal, potato, sugar beet, tomato, pea, leek, asparagus, fodder grasses and fodder clover.
  • Cereal is, for example, wheat, rice, corm, barley, oats, triticale and rye.
  • the plant products are in particular the harvested products of these plants, for example cereal grains and, in the case of corn, also the corncob, potatoes, sugar beets, tomatoes, peas, leek, asparagus and cut fodder grasses and fodder clover, for example hay.
  • the plants are selected from the group consisting of wheat, such as durum wheat or common wheat, barley, rye, triticale, oats, rice and corn.
  • the plant products are particularly preferably the harvested products of these plants, such as cereal grains.
  • the growth regulators (I) and/or (II) are used especially for reducing or preventing the contamination of wheat with the mycotoxins mentioned above.
  • the compounds (I) and/or (II) are used for reducing or preventing the contamination of plants and plant products with toxins selected from the group consisting of deoxynivalenol (DON), nivalenol (NIV) and zearalenone (ZEA).
  • DON deoxynivalenol
  • NAV nivalenol
  • ZAA zearalenone
  • the compounds of the formulae (I) and (II) are known and are generally used as growth regulators (growth retardants) in agriculture (see, for example, EP-A-123001, EP-A-126713, W. Rademacher, “Growth Retardants: Effects on Gibberellin Biosynthesis and Other Metabolic Pathways”, Annu. Rev. Plant. Mol. Biol. 2000, 51, 501-531).
  • the compounds of the formula (I) can be present either in the trione form (triketo form) I.a or in the tautomeric keto-enol forms I.b or I.c:
  • R 1 is preferably H or C 1 -C 4 -alkyl.
  • R 2 is preferably C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl and especially ethyl or cyclopropyl.
  • the salts of the acylcyclohexanedione compounds I where R 1 ⁇ H are the salts of monoanions, whereas in the case of R 1 ⁇ H they may be the salts both of the mono- and the dianions of these compounds.
  • the monoanions can be present either as carboxylate anions I.d or as enolate anions I.e or I.f:
  • both the carboxylate and the enolate groups are present.
  • Preferred cations in the salts of the compounds of the formula I are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, furthermore ammonium (NH 4 + ) and substituted ammonium, where one to four hydrogen atoms are replaced by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethyl-ammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium
  • Preferred cations are furthermore chlormequat [(2-chloro-ethyl)trimethylammonium], mepiquat (N,N-dimethylpiperidinium) and N,N-dimethyl-morpholinium.
  • Particularly preferred cations are the alkali metal cations, the alkali earth metal cations and the ammonium cation (NH 4 + ). It is in particular the calcium salt.
  • one of the radicals R 3 or R 4 is preferably C 1 -C 10 -alkyl and the other radical is preferably C 1 -C 10 -alkyl substituted by a halogen atom, preferably by a chlorine atom.
  • R 3 is methyl and R 4 is 2-chloroethyl.
  • R 3 and R 4 together form a bridging unit —(CH 2 ) 5 —.
  • the anions X ⁇ in the compounds II are selected from the group consisting of halide ions, sulfate ions and carbonate ions.
  • the anions X ⁇ in the compounds II are selected from the group consisting of halide ions, especially chloride, borates, especially pentaborate, and mixtures thereof.
  • X ⁇ is particularly preferably a halide anion and in particular chloride.
  • the quaternary ammonium compounds of the formula (II) are especially the salt of chlormequat (salt of 2-chloroethyltrimethylammonium), in particular chlormequat chloride (2-chloroethyltrimethylammonium chloride) or the salt of mepiquat (salt of 1,1-dimethylpiperidinium), in particular mepiquat chloride (1,1-dimethylpiperidinium chloride).
  • acylcyclohexanediones are used.
  • prohexadione, prohexadione-calcium, trinexapac and trinexapac-ethyl preference is given to prohexadione-calcium.
  • the use of compounds of the formulae (I) and/or (II) for reducing or preventing the contamination with the mycotoxins mentioned above is generally carried out by treating the plants or plant parts thereof or the plant products with these compounds.
  • the treatment of the plants or the plant products is preferably carried out by bringing the plant or the plant parts thereof or the plant product into contact with at least one compound selected from compounds of the formulae (I) and (II).
  • at least one of the compounds (I) and/or (II) is applied to the plant or plant parts thereof or to the plant product.
  • a plurality of compounds of the formulae (I) and/or (II) are employed, they can be applied in a mixture or separately.
  • the individual active substances can be employed simultaneously or—as part of a treatment sequence—staggered in succession, where in the case of successive application the application is preferably within an interval of a few hours to several weeks.
  • the treatment of the plants or plant parts or of the plant products can be both prophylactically and therapeutically, i.e. after an infection with harmful fungi. However, it is preferably prophylactically, i.e. before the infection by the corresponding species of harmful fungi.
  • the active compounds can be applied as such or in the form of their formulations or in the form of the use forms prepared therefrom, by spraying, atomizing, dusting, broadcasting or watering.
  • the use forms depend entirely on the intended purposes, especially on the species and cultivar of plant and on the plant part or plant product to which they are to be applied; in each case, the finest possible distribution of the active compounds employed according to the invention and also of the auxiliaries should be ensured.
  • the compounds of the formulae I and II mentioned are typically employed as formulations customary in the field of crop protection and the protection of supply products.
  • Customary formulations are, for example, solutions, emulsions, suspensions, dispersions, pastes, dusts, materials for broadcasting, powders and granules.
  • the formulations are prepared in a known manner, for example by extending the active compound with solvents and/or carriers, if desired with the use of emulsifiers and dispersants.
  • Solvents/auxiliaries suitable for this purpose are essentially:
  • Inert formulation auxiliaries suitable in particular for preparing directly sprayable solutions, emulsions, pastes or oil dispersions are essentially: mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylenes, paraffins, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones, such as cyclohexanone and isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil
  • coal tar oils and oils of vegetable or animal origin aliphatic, cyclic and aromatic hydrocarbons
  • Powders, materials for broadcasting and dusts can be prepared by mixing or jointly grinding the active substances with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphat
  • the formulations generally comprise the compounds (I) and/or (II) in a total amount of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, based on the total weight of the formulation.
  • Products (formulations) for dilution with water are, for example, water-soluble concentrates (SL), dispersible concentrates (DC), emulsifiable concentrates (EC), emulsions (EW, EO), suspensions (SC, OD), water-dispersible and water-soluble granules (WG, SG) and also water-dispersible and water-soluble powders (WP, SP).
  • Products (formulations) for direct application are, for example, dusts (DP), granules (GR, FG, GG, MG) and ULV solutions (UL).
  • Aqueous use forms can be prepared from storage-stable formulations, such as concentrated solutions, emulsion concentrates, suspensions, pastes, wettable powders (spray powders, oil dispersions) or water-dispersible granules, by addition of water, and they can be applied, for example, by spraying.
  • storage-stable formulations such as concentrated solutions, emulsion concentrates, suspensions, pastes, wettable powders (spray powders, oil dispersions) or water-dispersible granules, by addition of water, and they can be applied, for example, by spraying.
  • the compounds of the formulae (I) and/or (II) are dissolved as such or in an oil or solvent and can be homogenized in water using wetting agents, tackifier, dispersants or emulsifiers.
  • wetting agents wetting agents, tackifier, dispersants or emulsifiers.
  • concentrates from the active substance and wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, which concentrates are suitable for dilution with water.
  • the use forms will comprise the auxiliaries used in the storage-stable formulations.
  • the active compound concentrations in the preparations diluted with water may vary within relatively wide ranges. In general, they are between 0.0001 and 10% by weight, preferably between 0.01 and 1% by weight.
  • Oils of various types, wetting agents, adjuvants, fungicides, insecticides, bactericides, other growth regulators or else fertilizers can be added to the active compounds, if need be even immediately prior to application (tank mix). These agents can be added to the compositions used according to the invention in a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.
  • Suitable adjuvants in this sense are in particular: organically modified polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO/PO block polymers, for example Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates, for example Lutensol XP 80®; and sodium dioctylsulfosuccinate, for example Leophen RA®.
  • organically modified polysiloxanes for example Break Thru S 240®
  • alcohol alkoxylates for example Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®
  • EO/PO block polymers for example Pluronic RPE 2035® and Genapol B®
  • alcohol ethoxylates for example Lutensol XP 80®
  • the combined use of the compounds (I) and/or (II) with further active compounds customary in crop protection, for example with fungicides, can take place either by using a mixture of these active compounds (for example a joint formulation or a tank mix) or by successive application of the individual active compounds.
  • Particularly suitable is the use of the compounds (I) and/or (II) in combination with at least one fungicide.
  • the fungicides are preferably selected from the group consisting of metconazole, tebuconazole, prothioconazole, epiconazole, fenpropimorph, dimoxystrobin and kresoxim-methyl.
  • the fungicides are particularly preferably selected from the group consisting of metconazole, tebuconazole and prothioconazole.
  • the compounds of the formula (I) and/or (II) are used in the form of an aqueous spray liquor.
  • Application is preferably by spraying.
  • the spray liquor is applied either to the entire above-ground part of the plant or else only to individual plant parts, such as, flowers, fruits, leaves or individual shoots.
  • the choice of the individual plant parts to which the spray liquor is to be applied depends on the plant species and on its development stage. Application is preferably to the entire above-ground part of the plant or else to the parts which require particular protection against toxin contamination or which are preferably infected by trichothecene-forming fungi.
  • the compounds of the formulae (I) and/or (II) are employed in a total amount of from 5 to 3000 g/ha, preferably from 50 to 1000 g/ha and particularly preferably from 100 to 500 g/ha per season.
  • mixtures of compounds (I) and (II) are used for field application, their ratio is preferably from 2:1 to 1:30, particularly preferably from 1:1 to 1:20 and especially from 1:2 to 1:10, for example about 1:6.
  • the compounds (I) and/or (II) are preferably applied 1 to 5 times, particularly preferably 1 to 3 times and especially once or twice.
  • the compounds of the formulae (I) and/or (II) are used in the form of dusts.
  • the compounds of the formulae (I) and/or (II) are employed in a total amount of from 0.1 to 700 g, preferably from 0.5 to 120 g and particularly preferably from 1 to 60 g per metric ton of harvested material.
  • mixtures of compounds (I) and (II) are used for stored harvested material, their ratio is preferably from 1:10 to 10:1, particularly preferably from 1:5 to 10:1 and especially from 1:1 to 6:1, for example about 5:1.
  • the present invention furthermore provides a method for reducing or preventing the contamination of plants and plant products with toxins formed by trichothecene-producing fungi, where a plant, a plant part or a plant product is brought into contact with at least one compound selected from the group consisting of acylcyclohexane-diones of the formula (I) or salts thereof and quaternary ammonium compounds of the formula (II) or mixtures thereof.
  • the formation of trichothecene-toxins and other mycotoxins originating from trichothecene-producing harmful fungi is reduced considerably. This reduction is based not on a fungicidal action of the growth regulators used, which would result in the death of the toxin-producing harmful fungi, but, in particular, on the inhibition of the biosynthesis of trichothecenes and other mycotoxins in these harmful fungi. In this manner, it is possible to suppress contamination with mycotoxins of plants and plant products even in cases where the harmful fungi do not react or not sufficiently to the fungicides employed.
  • prohexadione-Ca results in a reduced DON content of the harvested wheat grains.
  • prohexadione-Ca used in addition to the fungicides employed in each case, results in a reduced contamination of the grains with DON compared to the treatment with the respective fungicides alone, in the case of a comparable Fusarium infection.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
US11/988,474 2005-07-19 2006-07-18 Use of Growth Regulators for Reducing or Preventing the Contamination of Plants and Vegetable Products by Trichothecene-Producing Mould Toxins Abandoned US20090131519A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102005033686.8 2005-07-19
DE102005033686 2005-07-19
PCT/EP2006/064367 WO2007009988A1 (de) 2005-07-19 2006-07-18 Verwendung von wachstumsregulatoren zur verringerung oder verhinderung der kontamination von pflanzen und pflanzenprodukten mit toxinen von trichothecen-produzierenden schimmelpilzen

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Cited By (2)

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US20100273652A1 (en) * 2009-04-27 2010-10-28 Bayer Cropscience Ag Use of 4-Aza Indole Derivatives for the Reduction of Mycotoxin Contamination
US20110177947A1 (en) * 2008-09-26 2011-07-21 Basf Se Use of Acylcyclohexanedione Carboxylic Acid or Salts Thereof in Combination with Acylcyclohexanedione Carboxylic Acid Esters for Improving the Development of Gramineous Plants

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5110618B2 (ja) * 2006-07-12 2012-12-26 クミアイ化学工業株式会社 マイコトキシン生合成阻害剤
EP2064952A1 (en) 2007-11-29 2009-06-03 Bayer CropScience AG Method for reducing mycotoxin contamination in maize

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US6022831A (en) * 1997-07-15 2000-02-08 Basf Corporation Control of Erwinia amylovora in plants
US20040241662A1 (en) * 2003-05-30 2004-12-02 Robey W. Wade Detecting microbial contamination in grain and related products

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JPH07223913A (ja) * 1994-02-14 1995-08-22 Nippon Soda Co Ltd 種子消毒剤
AU5971200A (en) * 1999-06-17 2001-01-09 Basf Aktiengesellschaft Method of increasing the resistance of cultivated plants to phytopathogen fungi
NZ540594A (en) * 2002-12-04 2008-03-28 Sankyo Agro Co Ltd Method of preventing wheat from mycotoxin contamination
AR056290A1 (es) * 2005-03-31 2007-10-03 Nippon Soda Co Metodo para inhibir la produccion de de micotoxina
CA2612110C (en) * 2005-06-30 2015-07-28 Syngenta Participations Ag Method of reducing mycotoxin contamination of the harvest
DK1906733T3 (da) * 2005-07-18 2012-12-17 Basf Se Kombineret anvendelse af metconazol og epoxiconazol til formindskelse eller forhindring af kontimination af korn med mykotosiner

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US6022831A (en) * 1997-07-15 2000-02-08 Basf Corporation Control of Erwinia amylovora in plants
US20040241662A1 (en) * 2003-05-30 2004-12-02 Robey W. Wade Detecting microbial contamination in grain and related products

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110177947A1 (en) * 2008-09-26 2011-07-21 Basf Se Use of Acylcyclohexanedione Carboxylic Acid or Salts Thereof in Combination with Acylcyclohexanedione Carboxylic Acid Esters for Improving the Development of Gramineous Plants
US9220262B2 (en) 2008-09-26 2015-12-29 Basf Se Use of acylcyclohexanedione carboxylic acid or salts thereof in combination with acylcyclohexanedione carboxylic acid esters for improving the development of gramineous plants
US20100273652A1 (en) * 2009-04-27 2010-10-28 Bayer Cropscience Ag Use of 4-Aza Indole Derivatives for the Reduction of Mycotoxin Contamination

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JP4769300B2 (ja) 2011-09-07
KR20080030032A (ko) 2008-04-03
KR101314462B1 (ko) 2013-10-10
BRPI0613408A2 (pt) 2011-01-11
JP2009501763A (ja) 2009-01-22
WO2007009988A1 (de) 2007-01-25
PL1909571T3 (pl) 2017-03-31
EP1909571B1 (de) 2016-09-07
EP1909571A1 (de) 2008-04-16

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